Triethylamine → HCID 21088664, Verbindung

HRID 350745Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 350745
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[O:11][C:12]=2[CH2:13][CH2:14][C:15]([OH:17])=O)=[CH:4][CH:3]=1.C(N(CC)CC)C.C(Cl)(=O)OCC.[NH2:37][C:38]1[CH:43]=[CH:42][C:41]([P:44](=[O:51])([O:48][CH2:49][CH3:50])[O:45][CH2:46][CH3:47])=[CH:40][CH:39]=1>O.O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[O:11][C:12]=2[CH2:13][CH2:14][C:15]([NH:37][C:38]2[CH:43]=[CH:42][C:41]([P:44]([O:48][CH2:49][CH3:50])([O:45][CH2:46][CH3:47])=[O:51])=[CH:40][CH:39]=2)=[O:17])=[CH:6][CH:7]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 273213Diethyl (4-aminophenyl)phosphonateHCID 21088670HCID 21088670, Verbindung

Produkt 1

HCID 21088664HCID 21088664, VerbindungAusbeute 36 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of 4-(4-chlorophenyl)-2-phenyl-5-oxazolepropionic acid (500 mg), triethylamine (230 mg) and tetrahydrofuran (10 ml) was added ethyl chlorocarbonate (250 mg) at −40° C., and the mixture was stirred for 1 hr. Diethyl 4-aminophenylphosphonate (420 mg) was added, and the mixture was stirred at room temperature for 5 hrs. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography and 3-[4-(4-chlorophenyl)-2-phenyl-5-oxazolyl]-N-[4-(diethylphosphono)phenyl]propionamide (295 mg, yield 36%) was obtained as colorless prism crystals from a fraction eluted with ethyl acetate-chloroform (1:1, volume ratio). melting point: 139–140° C. (recrystallized from dichloromethane-isopropyl ether).

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 5 hrs
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-80ed209e5d724ba0bae6bf557db3fb2a
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07183276B2

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